Tetrahydroharmine

Tetrahydroharmine

Names
IUPAC name (1R)-7-Methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
Systematic IUPAC name 7-Methoxy-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline
Other names 1,2,3,4-Tetrahydroharmine; Leptaflorine; 2,3,4,9-Tetrahydro-7-methoxy-1-methyl-1H-pyrido(3,4-b)indole
Identifiers
CAS Number	17019-01-1 N
3D model (Jmol)	Interactive image
3DMet	B02865
Abbreviations	THH
ChEBI	CHEBI:311931 Y
ChEMBL	ChEMBL129208 Y
ChemSpider	140510 Y
KEGG	C09243 Y
MeSH	Tetrahydroharmine
PubChem	159809
InChI InChI=1S/C13H16N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7-8,14-15H,5-6H2,1-2H3 Y Key: ZXLDQJLIBNPEFJ-UHFFFAOYSA-N Y InChI=1S/C13H16N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7-8,14-15H,5-6H2,1-2H3 Key: ZXLDQJLIBNPEFJ-UHFFFAOYSA-N
SMILES CC1c(c2CCN1)[nH]c3c2ccc(OC)c3
Properties
Chemical formula	C13H16N2O
Molar mass	216.28 g·mol−1
Basicity (pKb)	10.334
Pharmacology
Legal status	AU: S9 (Prohibited)
Hazards
Flash point	195.2 °C (383.4 °F; 468.3 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tetrahydroharmine (THH) is a fluorescent indole alkaloid that occurs in the tropical liana species Banisteriopsis caapi. THH weakly inhibits serotonin reuptake.

Two other harmala alkaloids in B. caapi, harmaline and harmine, are reversible inhibitors of monoamine oxidase A. Tetrahydroharmine, however, does not inhibit monoamine oxidase B.

Harmala alkaloids are considered Schedule 9 prohibited substances under the Poisons Standard (October 2015). A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.